Villa vacation rentals in Wailea, Wailea-Makena

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Top-rated villa rentals in Wailea, Wailea-Makena

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Guest favorite

A coastal view features tall palm trees swaying gently against a clear blue sky. The sandy beach stretches along the shoreline, leading to calm turquoise waters. In the distance, a glimpse of a distant landmass is visible, adding to the serene atmosphere.

Villa in Wailea-Makena

4.96 out of 5 average rating, 94 reviews

Luxury at it's Finest, Truly a Home away from Home

Remodeled in 2020, this 2 /2 Villa is located at Grand Champion Golf & Tennis Villas in the exclusive resort destination of Wailea, Maui. We have been named a Super Hosts on Airbnb due to the great amenities, comfort, safety, cleanliness and luxurious accommodations this Villa provides. Wailea is the Gold Coast of Maui, close to pristine beaches, shopping and dining and this is a legal, exclusive vacation rental. Spacious and luxurious, feel Refreshed and Anew in your Home away from Home!

Guest favorite

A modern kitchen is showcased with sleek white cabinetry and stainless steel appliances. A decorative rug runs across the floor, while fresh greenery and a welcome sign add a touch of warmth. Natural light fills the space, highlighting the inviting atmosphere.

Villa in Wailuku

4.96 out of 5 average rating, 206 reviews

Luxurious Two Bedroom near I’ao Valley w/ Haleakal

Enjoy Haleakalā views from this spacious 2BR villa at The Blue Door on Church Street, a restored 1930s plantation home in historic Wailuku. Featuring a King and Queen bed, full kitchen, spa-like bath with soaking tub, and a private deck. Walk to cafés, shops, and theaters, or take a short drive to ʻĪao Valley, beaches, and top Maui attractions. Includes modern comforts, air conditioning, parking, and an on-site infrared sauna for a relaxing retreat away from the crowds.

Guest favorite

The image displays a lush tropical landscape featuring a lagoon-style pool surrounded by palm trees and poolside seating. A sandy beachfront leads to tranquil ocean waters, with distant island views under a clear blue sky.

Villa in Lahaina

5 out of 5 average rating, 12 reviews

Westin Nanea Kaanapali Ocean Villa 2BR Sleeps 6

Submit your requested dates & I will check availability & respond if I can confirm this rental for you. 2 Bedroom Westin Nanea Ocean Villa at Kaanapali Beach on Maui Island in Hawaii; 1,260 SQ FT; SLEEPS UP TO 6 ADULTS All the luxuries & amenities of a Westin resort + comfort of a villa w/ furnished kitchen, in-room washer/dryer, private balcony. Resort activities; gym/spa; Pool. Actual villa unit is assigned at check-in and views will vary; Free self-parking

Superhost

An expansive swimming pool is surrounded by palm trees and vibrant tropical landscaping. Lounge chairs in soft pink are arranged around the pool, which features a scenic rock formation. The ocean is visible in the background, with gentle waves lapping at the shore.

Villa in Lahaina

4.92 out of 5 average rating, 24 reviews

Kaanapali Beach Club "Deluxe Ocean View"

**PLEASE ASK! We have many more weeks, dates and many GUARANTEED views!** Prices based on views, events, etc. **HOTEL TAX of approx 19.00 per night paid to resort upon check in.** Located on Maui's world famous Ka'anapali Beach. Vibrant tropical landscaping, first-rate amenities and exclusive array of leisure activities. Kaanapali Beach Club offers a one-acre swimming pool with separate kids pool, as well as calming outdoor whirlpool hot tubs. *Stock Photos

Guest favorite

A tranquil outdoor space features a shimmering pool surrounded by lounge chairs and tropical greenery. Tall palm trees sway gently in the breeze, while shaded cabanas provide comfortable areas for relaxation. The pathway is lined with flourishing plants, enhancing the serene ambiance.

Villa in Kihei

4.95 out of 5 average rating, 58 reviews

Modern 2 bedroom/2bath Villa near Beach!

Kick back and relax in this calm, stylish space. This Villa features 2 king suites, peek-a-boo ocean views, and private lanais off of each bedroom. The main living area is comprised of a great room with vaulted ceilings and a large island in the kitchen. Custom cabinetry houses all the essentials needed for cooking and relaxing while at the Villa. Dual king bed suites feature full baths with enclosed walk in showers and silent A/C units.

Guest favorite

A spacious living area showcases a blue front door that opens to a scenic view. A comfortable sofa and a decorative coffee table are positioned on a patterned rug. Natural light fills the room through large windows, enhancing the inviting ambiance.

Villa in Wailuku

4.92 out of 5 average rating, 236 reviews

Luxurious 1BR Near I'ao Valley, Bright and Modern!

Experience authentic Maui at The Blue Door on Church Street, a renovated 1930s plantation home in historic Wailuku. This one-bedroom villa features a King-sized Nectar bed, memory foam sleeper sofa, spa-like bath, and a fully equipped bar area. Enjoy the on-site infrared sauna and walk to cafés, restaurants, and shops. Centrally located near ʻĪao Valley, beaches, and top Maui attractions—your perfect base for adventure and relaxation.

Guest favorite

A modern living area features a gray sofa facing a sleek coffee table on a patterned rug. Large sliding glass doors reveal an outdoor dining space and view of palm trees and the ocean, enhancing the connection to the tropical surroundings.

Villa in Kihei

4.92 out of 5 average rating, 86 reviews

Exquisite Ocean View Villa across from the Beach

Enjoy a refreshing dip in the pool before kicking back on a premium white sandy beach. This stylish villa features a modern slate décor, state-of-the-art kitchen, private covered lanai, and tropical garden of mango and palm trees. The condo is part of an upscale property tucked away on a residential oceanfront side street. Surf schools, bicycle rentals, spa treatments, and farmer’s market are just around the corner.

Superhost

A spacious outdoor area features a private pool with clear blue water, framed by stone landscaping. An arched structure offers shade near the pool, and a red bowl sculpture adds a pop of color. Lush greenery surrounds the space, enhancing the serene environment.

Villa in Lahaina

4.86 out of 5 average rating, 79 reviews

Kaanapali Fairway Villa 3BR, 3BA.

Welcome to this Kaanapali Golf course 3 bedroom 3 bath bed and breakfast. Permit number BBWMT 2021/0003-159 Halelo. This beautiful Mediterranean home is conveniently located on hole number 5 of the Kaanapali Golf Course with a private pool, swim up bar, and ocean view. Recently renovated with many added amenities and features, please see in description below.

Guest favorite

A spacious outdoor area features a tranquil pool surrounded by sun loungers. Lush green grass and palm trees add to the tropical setting. The modern structure with a covered seating area provides shade and comfort, enhancing the space for relaxation and leisure.

Villa in Kihei

4.92 out of 5 average rating, 85 reviews

Ocean View 2BR Villa Steps To The Beach

Villa 4 is a 2 Bedroom, 2 Bathroom remodeled Villa with a spacious living room and ocean view patio. This Villa offers privacy and comfort set back in a tropical lush garden filled with mango and palm trees. This single story, stand-alone villa that is charming, convenient, and clean. Note: Hawaii GET, TA & MCTAT taxes of 17.962% are included in our prices.